From his debut, Callahan became the template for a new kind of movie cop: an antihero who does not hesitate to cross professional and ethical boundaries in pursuit of his own vision of justice, especially when the law is poorly served by an inept bureaucracy.

Callahan is often considered a film icon, so much so that his nickname, "Dirty Harry", has entered the lexicon as slang for ruthless police officers. All of the Dirty Harry films feature Callahan killing criminals, mostly in gunfights. Phrases he utters in armed stand-offs, Go ahead, make my day and [...] you've got to ask yourself one question: 'Do I feel lucky?' Well, do you, punk? have become iconic. As the 1971 film was criticized for carrying fascist, or at least authoritarian, undertones, the sequels attempted to be more balanced by pitting Harry against villains from a broader ideological spectrum; notably in 1973's Magnum Force, in which Harry is shown fighting vigilantism.[1]

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Callahan is an Inspector with the San Francisco Police Department, usually with the Homicide department, although for disciplinary or political reasons he is occasionally transferred to other less prominent units, such as Personnel (in The Enforcer) or Stakeout (in Magnum Force) or just sent out of town on mundane research assignments (in Sudden Impact). Callahan's primary concern is protecting and avenging the victims of violent crime. Though proficient at apprehending criminals, his methods are often unconventional; while some claim that he is prepared to ignore the law and professional and ethical boundaries, regarding them as needless red tape hampering justice, his methods are usually within the law – he takes advantage of situations that justify his use of deadly force, sometimes almost creating those situations. When a group of men holding hostages in a liquor store in The Enforcer demand a getaway car, Callahan delivers one by driving the car through the store's plate glass window and then shooting the robbers. Rather than following the rules of the police department, Callahan inserts himself into the scene of the event at a time when the imminent use of deadly force by the criminals justifies his use of deadly force against the criminals. Conversely, in Sudden Impact when he finds out that Jennifer Spencer (Sondra Locke), the person responsible for a series of murders in San Francisco and San Paulo, was a rape victim killing her unpunished rapists, he lets her go free, indicating that he feels her retribution was justified. In The Dead Pool Callahan shoots a fleeing and unarmed Mafia assassin in the back and kills the villain in the end with a harpoon knowing that the man's pistol is out of ammunition.

Callahan goes a step further in Dirty Harry, in which he shoots serial killer Charles "Scorpio" Davis after Davis surrenders and put his hands in the air. Determined to know the location of a 14-year-old girl that Davis has kidnapped and tortured, Callahan then presses his foot onto Davis' leg wound, ignoring Davis's pleas for a doctor and a lawyer until Davis gives up the location of the kidnapped girl. Callahan is later informed by the District Attorney that because Callahan kicked in the door of Davis' residence without a warrant, and because Davis' confession of the girl's location was made under the duress of torture, the evidence against him is inadmissible, and Davis has been released without charges filed against him. Callahan explains his outlook to the Mayor of San Francisco, who asks how Callahan ascertains that a man he had shot was intending to commit rape; the inspector responds, "When a naked man is chasing a woman through an alley with a butcher knife and a hard-on, I figure he isn't out collecting for the Red Cross."

While his partners and many other officers respect and admire Callahan, others see him as unfit to serve on the police force. He often clashes with superiors who dislike Callahan's methods, and judges and prosecutors are wary of handling his cases because of frequent violations of the Fourth Amendment and other irregularities. A police commissioner admits that Callahan's "unconventional methods ... get results", but adds that his successes are "more costly to the city and this department in terms of publicity and physical destruction than most other men's failures". (The publicity makes him well known; in Sudden Impact, the police chief of another city calls him "the famous Harry Callahan".) Callahan is often reprimanded, suspended, and demoted to minor departments. At the start of Magnum Force Lt. Briggs transfers him to stakeout. In The Enforcer Captain McKay assigns him to personnel. In Sudden Impact he is threatened with a transfer to traffic and being fired, and in The Enforcer he begins a 180-day suspension imposed by McKay. According to film critic Roger Ebert, "it would take an hour in each of these movies to explain why he's not in jail".[2]

The films routinely depict Callahan as being a skilled marksman and strong hand-to-hand combatant, killing at least one man with his bare hands. He is a multiple winner of the SFPD's pistol championship. In the five movies, Callahan is shown killing a combined total of 45 criminals, mostly with his trademark revolver, a Smith & Wesson Model 29.44 Magnum, which he describes as "the most powerful handgun in the world". He refuses to join the secret police death squad in Magnum Force, as he prefers the present system, despite its flaws, to the vigilante alternative. In his fight against criminals, however, including the fellow officers on the death squad, Callahan is merciless and shows no hesitation or remorse at killing them.

In Dirty Harry, several explanations are suggested for his nickname. When his partner Chico Gonzalez asks of its origins, Frank DiGiorgio says that "that's one thing about our Harry; [he] doesn't play any favorites. Harry hates everybody: Limeys, Micks, Hebes, Fat Dagos, Niggers, Honkies, Chinks, you name it." After being called to talk down a jumper, Callahan states he is known as Dirty Harry because he is assigned to "every dirty job that comes along". When Harry is ordered to deliver ransom money to Scorpio, Gonzalez opines "no wonder they call him Dirty Harry; [he] always gets the shit end of the stick". In Dirty Harry Gonzalez humorously suggests that Callahan's nickname may have an alternate origin given that he twice ends up peeking through a naked woman's window and later follows a suspect into a strip club.

The movies reveal little about Callahan's personal background. In the first film, Callahan tells his partner's wife that his wife was killed by a drunk driver. She appears in Magnum Force in an old photograph which Harry turns around. The doctor tending to him after the first film's bank robbery intimates that "us Potrero Hill boys gotta stick together". The first film's novelization explains that Callahan grew up in this neighborhood and describes a hostile relationship between the police and the residents. Callahan recalls once throwing a brick at a cop, who picked it up and threw it back at him. The following sequels show that Harry lives within the city limits in a small studio apartment on Jackson St. in the Nob Hill area, so unfamiliar with his neighbours that they refer to him only as 'the cop who lives upstairs'. In Magnum Force Harry's friend Charlie McCoy says "We should have done our 20 in the Marines", indicating that they served (or could/should have served) together in the armed forces. In The Dead Pool, a coffee mug on Harry's desk at the police station bears the United States Marine Corps seal and in The Enforcer he is already checked out on the LAWS rocket, a USMC weapon. His hobbies appear to consist of target shooting and playing pool (which we see him doing in The Enforcer). He appears to subsist on a diet of only hot dogs, hamburgers and strong black coffee which he takes without sugar and is so unchanging that he simply orders 'The usual' from the staff off his regular eateries (in The Dead Pool he samples his girlfriend's unknown dessert but doesn't have one himself). He drinks beer (and on one occasion apple juice) and both runs and weightlifts in the gym. In Sudden Impact he acquires a pet bulldog called 'Meathead' but there is no sign of him in The Dead Pool.

Callahan's signature weapon is a Smith & Wesson Model 29.44 Magnumrevolver, which he describes as "the most powerful handgun in the world" and uses in all of the films. The gun's prominence in the films instantly popularized it. Callahan states the use of a "Light Special", .44 Special loads (a reference to the fact that .44 special cartridges can be fired in .44 magnum handguns), that he loads himself because it gives him "better accuracy and control in a gun this size," like using wadcutters in a .357 Magnum. In the audio commentary on Magnum Force DVD (Warner Bros. Entertainment, 2001), John Milius (who wrote the story and co-wrote the screenplay), said that this was misinterpreted during filming, that "it's really not supposed to be a light Special, it's just supposed to be a little lighter .44 Magnum load." implying he uses a specially prepared Magnum round firing a slightly less heavy bullet. This would corroborate his statement in The Enforcer that he favours the gun largely for penetration. In one film, Harry's partner Frank DiGiorgio, refers to Harry's gun as a "pocket-cannon".

Callahan loses hold of his sidearm four times during the course of the series; first in Dirty Harry when Scorpio tells him to take it out and throw it when he is confronted at the cross in the park, in Magnum Force, second in Sudden Impact, then in The Dead Pool. In The Enforcer, Callahan doesn't lose it, however he doesn't employ it to kill the final villain (in favor of a portable rocket launcher). Additionally, in Sudden Impact, Callahan temporarily upgraded to a .44 Automag. Contrary to popular belief, it was not an AMT firearm, but an original AMP AutoMag built specifically for that film.[3]

In Dirty Harry, he used a Winchester Model 70 bolt action rifle in .458 Winchester Magnum for the night gunfight with the Scorpio Killer and used a switchblade during his second encounter with Scorpio. Harry also uses a Colt Python revolver to obtain ballistics evidence in Magnum Force. Other weapons Callahan uses initially in the final climax of other films include a bomb, an M72 LAW rocket launcher and a harpoon.[4] In Dirty Harry the San Francisco police chief comments on Callahan's fondness for overkill observing that he "Likes an edge". Callahan responds that "I'll take all the edge I can get".

It is a recurring theme in the Dirty Harry movies that Callahan has a high turnover of partners; most are killed or wounded while working with him. In Dirty Harry, he mentions two unseen partners named Fanducci and Dietrich; Dietrich is in the hospital having been shot, while Fanducci is dead (in The Enforcer, it is referenced that Fanducci was killed in 1968). His partner in Dirty Harry, Chico Gonzalez, is shot by Scorpio and though he survives, he decides to quit the police (in Magnum Force, Harry remarks that Gonzalez became a college teacher after leaving the police force). His partner in Magnum Force, Earlington "Early" Smith is killed by a bomb planted in his mailbox. Kate Moore in The Enforcer is killed by terrorists while saving Callahan's life. She had previously cited to Harry the names of previous dead officers (Fanducci and Smith) to demonstrate that she is aware of the risks of being his partner. In Sudden Impact, Horace King is murdered by criminals who were waiting for Harry in his hotel room. Occasional Callahan partner Frank DiGiorgio was also killed, albeit whilst working with another officer. Of all Callahan's partners seen on screen, Al Quan and Gonzalez are the only two to survive.

Another theme explored in several movies is Callahan being assigned a partner he would instinctively resent being paired with, Chico Gonzalez because he is a rookie college graduate, and Kate Moore because she is a woman. However, they eventually earn his respect and both go on to save Harry's life.

In Dirty Harry we learn that Callahan's unnamed wife has recently died, her picture still on display in his apartment. In Magnum Force he begins a relationship with Sunny, an Oriental woman who is one of his neighbours and asks to go to bed with him on their first meeting. In Sudden Impact he establishes a sexual relationship with vigilante Jennifer Spencer although it is uncertain if this goes any further, Spencer commenting 'Neither of us want to be alone tonight'. In The Dead Pool he romances news reporter Samantha Walker and they are last seen walking away together at the end of the film

I know what you're thinking: 'Did he fire six shots or only five?' Well, to tell you the truth, in all this excitement I've kinda lost track myself. But being as this is a .44 Magnum, the most powerful handgun in the world, and would blow your head clean off, you've got to ask yourself one question: 'Do I feel lucky?' Well, do you, punk?

The former phrase was borrowed by US PresidentRonald Reagan in a March 1985 speech to the American Business Conference. Promising to veto any proposed tax rises, he challenged those who wanted them to: "Go ahead, make my day." It has also given its name to a law in several US states, the Make My Day Law, which protects homeowners who use lethal force against intruders.

Callahan uses different pairs of sunglasses throughout the series. His sunglasses in Magnum Force are the Ray-Ban Balorama.[11] In The Enforcer, he uses Ray-Ban B&LAviator Style A. In Sudden Impact, he wears Gargoyles ANSI sunglasses.[12]